Substituent-dependent disassembly of self-immolative dendrimers

Abstract

Self-immolative dendrimers are tree-like platforms, which can spontaneously release all their end-group molecules through a single activation event at the dendrimer’s focal point. This triggering event induces domino-like fragmentations, which leads to complete disassembly of the dendrimer into its separate building blocks. In this report, we demonstrate a simple approach to control the disassembly-rate of self-immolative dendrimers. Two types of dendrons were synthesized. One with a methyl substituent on the benzene building-block and the other with ethylcarboxy-ester. The dendrons (first- and second-generation) with electron-withdrawing substituents showed approximately 30 times faster disassembly-rate than dendrons with methyl substituents.